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US20060069266A1 - Hydroxy amide acetals - Google Patents

Hydroxy amide acetals Download PDF

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US20060069266A1
US20060069266A1 US11/241,489 US24148905A US2006069266A1 US 20060069266 A1 US20060069266 A1 US 20060069266A1 US 24148905 A US24148905 A US 24148905A US 2006069266 A1 US2006069266 A1 US 2006069266A1
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alkyl
hydroxy
alkynyl
alkenyl
aryl
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US7148316B2 (en
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Neville Everton Drysdale
Laura Ann Lewin
Robert Barsotti
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Axalta Coating Systems IP Co LLC
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Assigned to U.S. COATINGS IP CO. LLC reassignment U.S. COATINGS IP CO. LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: E. I. DU PONT DE NEMOURS AND COMPANY
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Definitions

  • the present invention relates to the preparation of hydroxy-functionalized amide acetals.
  • Amide acetals have been used for example in copolymerization with polyisocyanates as disclosed in U.S. Pat. No. 4,721,767.
  • Cross-linked amide acetal based coating compositions dry and cure rapidly without the potential problems created by VOC emissions. Such coatings can be very useful, for example, in the automotive coatings industry.
  • Hydroxy-functionalized amide acetals find use in cross-linkable coatings.
  • CA 132: 280540 an anonymous disclosure, alluded to the potential preparation of hydroxy amide acetals from epoxides and oxazolines but did not include how to make these, nor provide any experimental results.
  • the syntheses of these materials from hydroxy acids, esters or from lactone and beta-dihydroxyamines has not be disclosed, nor has experimental data been shown elsewhere in support of the composition of these compounds.
  • the present invention relates to hydroxy amide acetals of the formula wherein R 42 —R 49 independently represent a hydrogen, C 1 -C 20 alkyl, C 1 -C 20 alkenyl, C 1 -C 20 alkynyl, C 1 -C 20 aryl, C 1 -C 20 alkyl ester, or C 1 -C 20 aralkyl group, said alkyl, alkenyl, alkynyl, aryl, or aralkyl may each have one or more substituents selected from the groups consisting of halo, alkoxy, imino, and dialkylamino,
  • R 41 is (CR 50 R 51 ) n —OH, wherein R 50 and R 51 independently represent a hydrogen, C 1 -C 20 alkyl, C 1 -C 20 alkenyl, C 1 -C 20 alkynyl, C 1 -C 20 aryl, C 1 -C 20 alkyl ester, or C 1 -C 20 aralkyl group ; and
  • n 1-10.
  • the present invention further provides a process for forming a hydroxy amide acetal, said process comprising reacting a bis-(beta hydroxyl)amine with a hydroxy-containing moiety to form a hydroxy amide acetal of the formula wherein R 42 —R 49 independently represent a hydrogen, C 1 -C 20 alkyl, C 1 -C 20 alkenyl, C 1 -C 20 alkynyl, C 1 -C 20 aryl, C 1 -C 20 alkyl ester, or C 1 -C 20 aralkyl group, said alkyl, alkenyl, alkynyl, aryl, or aralkyl may each have one or more substituents selected from the groups consisting of halo, alkoxy, imino, and dialkylamino;
  • R 41 is (CR 50 R 51 ) n —OH, wherein R 50 and R 51 independently represent a hydrogen, C 1 -C 20 alkyl, C 1 -C 20 alkenyl, C 1 -C 20 alkynyl, C 1 -C 20 aryl, C 1 -C 20 alkyl ester, or C 1 -C 20 aralkyl group; and
  • n 1-10.
  • the invention further relates to products made by the process disclosed.
  • the present invention relates to a process for the preparation of hydroxy amide acetals.
  • Amide acetals have the general formula General processes for producing amide acetals are disclosed in co-owned and co-pending U.S. Patent Publication 2005-007461 and U.S. patent application Ser. No. 10/960,656. As disclosed in these applications, amide acetals can also be represented by the formula
  • R 42 —R 49 independently represent a hydrogen, C 1 -C 20 alkyl, C 1 -C 20 alkenyl, C 1 -C 20 alkynyl, C 1 -C 20 aryl, C 1 -C 20 alkyl ester, or C 1 -C 20 aralkyl group, said alkyl, alkenyl, alkynyl, aryl, or aralkyl may each have one or more substituents selected from the groups consisting of halo, alkoxy, imino, and dialkylamino; and, R 41 is (CR 50 R 51 ) n —OH, wherein R 50 and R 51 independently represent a hydrogen, C 1 -C 20 alkyl, C 1 -C 20 alkenyl, C 1 -C 20 alkynyl, C 1 -C 20 aryl, C 1 -C 20 alkyl ester, or C 1 -C 20 aralkyl group ; and where n is 1-10. It is
  • hydroxy functionalized amide acetals are readily synthesized by reacting hydroxy-containing moieties, including but not limited to hydroxy acids, hydroxy esters or lactones, with beta-dihydroxyamines. More specifically, this involves reacting, for example, a bis-(beta hydroxy)amine of the general formula
  • n is generally 1 to 10 and R is any C 1 to C 10 alkyl group; or with a lactone of the formula where n is 2 to 10; to form with all the R groups as defined above.
  • the reactants are added together with or without a common solvent (e.g., and heated to a gentle reflux until the reaction is complete (generally 12-24 hours) and the water formed by the reaction is distilled off and removed.
  • a solvent e.g., it is desirable to use an azeotropic solvent such as xylenes or toluene.
  • the materials made by the process described find use in a variety of end-uses, including but not limited to components in coatings for automotive and architectural structures.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Polyamides (AREA)

Abstract

The present invention relates to the preparation of hydroxy-functionalized amide acetals from bis-(beta hydroxy)amines and hydroxyl containing moieties.

Description

    CROSS REFERENCE TO RELATED APPLICATION
  • This application claims the benefit of U.S. Provisional Application 60/615,360, filed Sep. 30, 2004.
    • FIELD OF THE INVENTION
  • The present invention relates to the preparation of hydroxy-functionalized amide acetals.
    • BACKGROUND OF THE INVENTION
  • Amide acetals have been used for example in copolymerization with polyisocyanates as disclosed in U.S. Pat. No. 4,721,767. Cross-linked amide acetal based coating compositions dry and cure rapidly without the potential problems created by VOC emissions. Such coatings can be very useful, for example, in the automotive coatings industry.
  • Co-owned and co-pending US Patent Publication 2005-007461 describes polymeric compositions containing amide acetal groups, which are crosslinked by hydrolyzing the amide acetal groups, and subsequently reacting the hydroxyl groups and/or the amine functions that are formed to crosslink the composition.
  • Co-owned and co-pending U.S. patent application Ser. No. 10/960,656 describes a catalytic process for making amide acetals from nitrites and diethanolamines.
  • Hydroxy-functionalized amide acetals find use in cross-linkable coatings. CA 132: 280540, an anonymous disclosure, alluded to the potential preparation of hydroxy amide acetals from epoxides and oxazolines but did not include how to make these, nor provide any experimental results. However, the syntheses of these materials from hydroxy acids, esters or from lactone and beta-dihydroxyamines, has not be disclosed, nor has experimental data been shown elsewhere in support of the composition of these compounds.
    • SUMMARY OF THE INVENTION
  • The present invention relates to hydroxy amide acetals of the formula
    Figure US20060069266A1-20060330-C00001
    wherein R42—R49 independently represent a hydrogen, C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 aryl, C1-C20 alkyl ester, or C1-C20 aralkyl group, said alkyl, alkenyl, alkynyl, aryl, or aralkyl may each have one or more substituents selected from the groups consisting of halo, alkoxy, imino, and dialkylamino,
  • R41 is (CR50R51)n—OH, wherein R50 and R51 independently represent a hydrogen, C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 aryl, C1-C20 alkyl ester, or C1-C20 aralkyl group ; and
  • n is 1-10.
  • The present invention further provides a process for forming a hydroxy amide acetal, said process comprising reacting a bis-(beta hydroxyl)amine with a hydroxy-containing moiety to form a hydroxy amide acetal of the formula
    Figure US20060069266A1-20060330-C00002
    wherein R42—R49 independently represent a hydrogen, C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 aryl, C1-C20 alkyl ester, or C1-C20 aralkyl group, said alkyl, alkenyl, alkynyl, aryl, or aralkyl may each have one or more substituents selected from the groups consisting of halo, alkoxy, imino, and dialkylamino;
  • R41 is (CR50R51)n—OH, wherein R50 and R51 independently represent a hydrogen, C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 aryl, C1-C20 alkyl ester, or C1-C20 aralkyl group; and
  • n is 1-10.
  • The invention further relates to products made by the process disclosed.
    • DETAILS OF THE INVENTION
  • The present invention relates to a process for the preparation of hydroxy amide acetals. Amide acetals have the general formula
    Figure US20060069266A1-20060330-C00003
    General processes for producing amide acetals are disclosed in co-owned and co-pending U.S. Patent Publication 2005-007461 and U.S. patent application Ser. No. 10/960,656. As disclosed in these applications, amide acetals can also be represented by the formula
    Figure US20060069266A1-20060330-C00004
  • wherein R42—R49 independently represent a hydrogen, C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 aryl, C1-C20 alkyl ester, or C1-C20 aralkyl group, said alkyl, alkenyl, alkynyl, aryl, or aralkyl may each have one or more substituents selected from the groups consisting of halo, alkoxy, imino, and dialkylamino; and, R41 is (CR50R51)n—OH, wherein R50 and R51 independently represent a hydrogen, C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 aryl, C1-C20 alkyl ester, or C1-C20 aralkyl group ; and where n is 1-10. It is more typical that R42—R49 each independently represent hydrogen and C1-C10 alkyl groups.
  • These and other features and advantages of the present invention will be more readily understood, by those of ordinary skill in the art, from a reading of the following detailed description. It is to be appreciated those certain features of the invention, which are, for clarity, described above and below in the context of separate embodiments, may also be provided in combination in a single embodiment. Conversely, various features of the invention that are, for brevity, described in the context of a single embodiment, may also be provided separately or in any sub-combination. In addition, references in the singular may also include the plural (for example, “a” and “an” may refer to one, or one or more) unless the context specifically states otherwise.
  • It has been discovered that hydroxy functionalized amide acetals are readily synthesized by reacting hydroxy-containing moieties, including but not limited to hydroxy acids, hydroxy esters or lactones, with beta-dihydroxyamines. More specifically, this involves reacting, for example, a bis-(beta hydroxy)amine of the general formula
    Figure US20060069266A1-20060330-C00005
      • where R42—R49 are defined as above, with a hydroxy acid of the formula HO—(CR50R51)n—C(O)OH, where n is generally 1 to 10;
        or with a hydroxy ester of the formula
  • HO—(CR50R51)n—C(O)OR, where n is generally 1 to 10 and R is any C1 to C10 alkyl group;
    or with a lactone of the formula
    Figure US20060069266A1-20060330-C00006
    where n is 2 to 10; to form
    Figure US20060069266A1-20060330-C00007
    with all the R groups as defined above.
  • Generally, the reactants are added together with or without a common solvent (e.g., and heated to a gentle reflux until the reaction is complete (generally 12-24 hours) and the water formed by the reaction is distilled off and removed. If a solvent is used, it is desirable to use an azeotropic solvent such as xylenes or toluene.
  • The materials made by the process described find use in a variety of end-uses, including but not limited to components in coatings for automotive and architectural structures.
  • The use of numerical values in the various ranges specified in this application, unless expressly indicated otherwise, are stated as approximations as though the minimum and maximum values within the stated ranges were both preceded by the word “about.” In this manner slight variations above and below the stated ranges can be used to achieve substantially the same results as values within the ranges. Also, the disclosure of these ranges is intended as a continuous range including every value between the minimum and maximum values.
  • Unless otherwise stated, all chemicals and reagents were used as received from Aldrich Chemical Co., Milwaukee, Wis.
    • EXAMPLES Example 1
  • In a 500 mL RB flask equipped with a Dean Starke trap, glycolic acid (76.0 g, 1.00 mol), diisopropanolamine (133 g, 1.00 mol) and xylenes (100 mL) were added. The reaction content was heated to a gently reflux. After ˜16 hours 22.73 g of water was collected. The trap was removed and the xylenes removed under vacuum and the reaction content vacuum distilled.
    Fraction Weight Comment
    1 12.80 Almost all product
    2 51.18 Almost all product
    3 57.70 almost all product
    4 31.58 Contaminated product
    • Example 2
  • In a 500 mL RB flask equipped with a Dean Starke trap, E-caprolactone (109.60, 0.96 mol), diisopropanolamine (129.9 g, 0.96 mol) and xylenes (100 mL) were added. The reaction content was heated to a gently reflux. After ˜16 hours 3.92 g of water was collected. The trap was removed and the xylenes removed under vacuum and the reaction content vacuum distilled. NMR (proton) of the second fraction (47.22 g) showed it to contain product although contaminated.

Claims (6)

1. An hydroxy amide acetal composition of the formula
Figure US20060069266A1-20060330-C00008
wherein R42—R49 independently represent a hydrogen, C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 aryl, C1-C20 alkyl ester, or C1-C20 aralkyl group, said alkyl, alkenyl, alkynyl, aryl, or aralkyl may each have one or more substituents selected from the groups consisting of halo, alkoxy, imino, and dialkylamino;
R41 is (CR50R51)n—OH, wherein R50 and R51 independently represent a hydrogen, C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 aryl, C1-C20 alkyl ester, or C1-C20 aralkyl group ; and
n is 1-10.
2. The hydroxy amide acetal of claim 1, wherein R42—R49 each independently represent hydrogen and C1-C10 alkyl groups.
3. A process for forming a hydroxy amide acetal, said process comprising reacting a bis-(beta hydroxyl)amine with a hydroxy-containing moiety to form a hydroxy amide acetal of the formula
Figure US20060069266A1-20060330-C00009
wherein R42—R49 independently represent a hydrogen, C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 aryl, C1-C20 alkyl ester, or C1-C20 aralkyl group, said alkyl, alkenyl, alkynyl, aryl, or aralkyl may each have one or more substituents selected from the groups consisting of halo, alkoxy, imino, and dialkylamino;
R41 is (CR50R51)n—OH, wherein R50 and R51 independently represent a hydrogen, C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 aryl, C1-C20 alkyl ester, or C1-C20 aralkyl group ; and
n is 1-10.
4. The process of claim 3, wherein R42—R49 each independently represent hydrogen and C1-C10 alkyl groups.
5. The process of claim 3, wherein the hydroxy containing moiety is selected from the group consisting of hydroxy acids, hydroxy esters and lactones.
6. A product of the process of claim 4.
US11/241,489 2004-09-30 2005-09-30 Hydroxy amide acetals Expired - Lifetime US7148316B2 (en)

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US61536004P 2004-09-30 2004-09-30
US61535804P 2004-09-30 2004-09-30
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090227794A1 (en) * 2004-11-09 2009-09-10 Bristol-Myers Squibb Company Crystalline materials of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1h-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070049752A1 (en) * 2005-08-23 2007-03-01 Drysdale Neville E Preparation of 2,6-dioxa-7-aza-bicyclo[2.2.2] octanes
US7812173B2 (en) * 2005-08-23 2010-10-12 E.I. Du Pont De Nemours And Company Tetrahydro-1,8-dioxa-4a-aza-naphthalenes in coating applications
CN111013979A (en) * 2019-11-22 2020-04-17 圣象（江苏）木业研究有限公司 Paint process of visible angle color-changing wood floor

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050222425A1 (en) * 2003-10-09 2005-10-06 Adelman Douglas J Process for making amide acetals

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050222425A1 (en) * 2003-10-09 2005-10-06 Adelman Douglas J Process for making amide acetals

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090227794A1 (en) * 2004-11-09 2009-09-10 Bristol-Myers Squibb Company Crystalline materials of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1h-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione

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US7148316B2 (en) 2006-12-12
JP2008514728A (en) 2008-05-08
MX2007003563A (en) 2007-05-18
EP1805185A1 (en) 2007-07-11

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